The Founder’s Dilemma: The Business Of Hard Choices

Dear Reader,

Brutal dilemmas are the fabric of being a founder. It’s the grit driving each decision, the resilience to endure the fallout, and the tenacity to continue despite overwhelming odds. (tweet this)

Book: The Founder’s Dilemmas by Noam Wasserman – a decade of research delves into the dirty reality of control.

Last week: Founder Glow Up: With All Your Sh*t, You’re Still The Best CEO

Behind every tough choice is a personal sacrifice, but not every decision qualifies as a dilemma. It’s where both options carry significant weight and consequences that truly define it. More often than not; it’s deeply personal.

Before the grind, the glow up, the inspo-quote on Insta, is the core of the Founder’s Dilemma. It’s not about whether you should work harder or longer; you should; it’s about which mountain to climb first. The Founder’s Dilemma is the tension between equally compelling options, the fork in the road.

It’s the oh f*ck moment when you’re about to make (or have just made) that pivotal decision (that might actually be a pivot!). It’s the second-guessing, the playing out scenarios over and over. Where the weight of the future hangs on this single choice, and you question everything. Your qualifications, the risks, and if it might all be too much.

Yes, but: for many founders, decisions don’t always appear as clear, dichotomous choices, many don’t even see or acknowledge that a dilemma even exists. It might be the illusion of a predestined route, the blind faith in a single solution, the sheer oblivion to potential forks, or the biases influencing their judgment – whatever the reason, you are totally oblivious.

Recognizing a dilemma exists is the first step. Exceptional founders not only see the dilemma, understand it as a defining moment but also have the introspective capacity to take action.

Yes, but: some trailblazers seem to win precisely because they go all-in on one path. Whether it is ignorance, inexperience, or arrogance, occasionally, this audacious leap becomes legendary, the outlier that made it is still an outlier. Being exceptional might just mean being that fortunate outlier.

Hard choices and grit are intricately linked. When we talk about grit, we often think of the resilience to keep pushing forward. As a founder, you likely didn’t know there is an Act One to grit.

Decisional Grit: When you’re cornered, when the right choice and the easy one diverge. Grit is the enabler of hard decisions. The courage to decide, the conviction to execute, knowing there’s a chance for failure but betting it all on red.

Endurance Grit: More than “toughing it out” this is about adapting, learning, and strengthening through challenges. This grit, most importantly, comes after the tough decisions.

Reed Hastings of Netflix (old enough to remember “Qwikstergate“). His decision to separate DVD rentals and streaming was audacious. The backlash was immediate and massive. Yet, despite the catastrophe his vision of a streaming future never changed. That’s the Founder’s Dilemma in action.

The classic Founder’s Dilemma is rich vs king. Do you want to maximize financial gain (become “rich”) or retain control over decision-making (be the “sovereign”). Most founders naturally want both, but in most cases, founders have to choose one.

Founder’s Dilemma is whether to bring on a co-founder; 50% of something or 100% of nothing? Should you bring on a high-performing CTO and make room, give up some control and equity, or do you hire employees on UpWork and retain full command. This is the dilemma of control vs collaboration or realizing potential versus embracing certainty.

Founder’s Dilemma is the decision when you feel like you have some traction, but no investors are interested. Do you mortgage the house? Do you risk everything? Do you keep going? Do you pivot?

It’s the late-night decision of whether to send that email now or wait until morning. It’s that ‘want’ to e-mail a prospect with a lower price, to accept a customer you know is going to be a nightmare, to be transparent in your investor update, to give the hard feedback to an employee. It’s the dilemma of choosing between being home for dinner or keep working. It’s the allocation of budget to a marketing campaign that might just change everything. Daily dilemmas come in all sizes, at all moments, they are the heartbeat of a founder’s journey.

Founder’s Dilemma isn’t about poor decision-making. A founder who chooses to ignore ‘go to market’ and instead races their time and budget into engineering isn’t facing a dilemma; that’s a misstep. It was inexperience and lack of capability to recognize there might be a better way. Do not confuse them.

All of this to say: the Founder’s Dilemma is more than just decision making. It’s the fortitude behind them, the aftermath, and the evolution that ensues. It’s about making difficult calls, owning the results, and leveraging adversity. That’s the real Founder’s Dilemma, and it’s the business of hard choices.

Brutal dilemmas; That’s how legends are born.

Here’s to the dilemmas that only you know exist, and the successes they might lead to.

— James

(LinkedIn | Twitter | Tiktok)